3,4,5,6-Tetrahydrophthalic anhydride → HCID 14423596, compound

HRID 1199613Notes

Reaction equation

HRID 1199613 reaction equation
[NH2:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.[C:21]1(=O)[O:26][C:24](=[O:25])[C:23]2[CH2:27][CH2:28][CH2:29][CH2:30][C:22]1=2>C(O)(=O)C>[F:20][C:3]1[C:2]([N:1]2[C:24](=[O:25])[C:23]3[CH2:27][CH2:28][CH2:29][CH2:30][C:22]=3[C:21]2=[O:26])=[CH:19][C:6]2[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 14423583HCID 14423583, compound

Product 1

HCID 14423596HCID 14423596, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-amino-7-fluoro-4-(pyridin-2-ylmethyl)-2H-1,4-benzoxazin-3(4H)-one (2 g), 3,4,5,6-tetrahydrophthalic anhydride (1.2 g) and acetic acid (50 ml) was heated under reflux for 1 hour. The acetic acid was distilled off under a reduced pressure, and the residue was dissolved in toluene (100 ml), washed in a saturated aqueous solution of sodium bicarbonate and then in water, and dried over anhydrous sodium sulfate. The toluene was distilled off under a reduced pressure, and the resultant residue was recrystallized from ethanol, whereby the aimed product, namely, 7-fluoro-4-(pyridin-2-ylmethyl)-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (2.4 g) was obtained. m.p. 188°-190° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. distillationThe acetic acid was distilled off under a reduced pressure
  4. dissolutionthe residue was dissolved in toluene (100 ml)
  5. washwashed in a saturated aqueous solution of sodium bicarbonate
  6. dry with materialin water, and dried over anhydrous sodium sulfate
  7. distillationThe toluene was distilled off under a reduced pressure
  8. customthe resultant residue was recrystallized from ethanol, whereby the aimed product

Sources & evidence

ORD record
ord-32bdb40ad5084a049b34f8fa13613850
Source dataset
uspto-grants-1990_02
Patent number
US04902335

Reaction notes

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